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Florence had been under a republican government since 1494, when the leading Medici family and its supporters had been driven from power.During this time, Machiavelli thrived under the patronage of the Florentine (or chief administrator for life) Piero Soderini.
In 1512, however, with the assistance of papal troops, the Medici defeated the republic's armed forces and dissolved the government.
Machiavelli was a direct victim of the regime change: he was initially placed in a form of internal exile and, when he was (wrongly) suspected of conspiring against the Medici in 1513, he was imprisoned and tortured for several weeks.
Machiavelli's critique of utopian philosophical schemes (such as those of Plato) challenges an entire tradition of political philosophy in a manner that that commands attention and demands consideration and response.
Finally, a new generation of so-called “neo-Roman” political theorists (such as Philip Pettit , Quentin Skinner  and Maurizio Viroli [1999 ]) finds inspiration in Machiavelli’s version of republicanism.
That question might naturally and legitimately occur to anyone encountering an entry about him in an encyclopedia of philosophy.
Certainly, Machiavelli contributed to a large number of important discourses in Western thought—political theory most notably, but also history and historiography, Italian literature, the principles of warfare, and diplomacy.(Many of his colleagues in the republican government were quickly rehabilitated and returned to service under the Medici.) Originally written for presentation to Giuliano de'Medici (who may well have appreciated it), the dedication was changed, upon Giuliano's death, to Lorenzo de'Medici, who almost certainly did not read it when it came into his hands in 1516.Meanwhile, Machiavelli's enforced retirement led him to other literary activities.Many authors (especially those who composed mirror-of-princes books or royal advice books during the Middle Ages and Renaissance) believed that the use of political power was only rightful if it was exercised by a ruler whose personal moral character was strictly virtuous.Thus rulers were counseled that if they wanted to succeed—that is, if they desired a long and peaceful reign and aimed to pass their office down to their offspring—they must be sure to behave in accordance with conventional standards of ethical goodness.Even if Machiavelli grazed at the fringes of philosophy, the impact of his extensive musings has been widespread and lasting.The terms “Machiavellian” or “Machiavellism” find regular purchase among philosophers concerned with a range of ethical, political, and psychological phenomena, regardless of whether or not Machiavelli himself invented “Machiavellism” or was in fact a “Machiavellian” in the sense commonly ascribed to him.He tends to appeal to experience and example in the place of rigorous logical analysis.Yet there are good reasons to include Machiavelli among the greatest of political philosophers, some of which are internal to his writings.For the next fourteen years, Machiavelli engaged in a flurry of diplomatic activity on behalf of Florence, traveling to the major centers of Italy as well as to the royal court of France and to the imperial curia of Maximilian.A large body of extant letters, dispatches, and occasional writings testify to his political assignments as well as to his acute talent for the analysis of personalities and institutions.